Chilavert grew up in Luque, Gran Asunción,[10] in a poor family, and walked barefoot until the age of seven.[11] His parents were Catalino Chilavert, a state bureaucrat, and Nicolasa González. At the age of five, he had three siblings and two responsibilities: to milk the cows and to sell the milk in Ñu Guazú, a rural suburb of Luque.[12] One of his siblings, Rolando Chilavert, is also a football player.[citation needed]

He later moved to Spain, where he played for Real Zaragoza. In 1988, whilst Chilavert played for Real Zaragoza, he stated that "the fans used to freak out" when he would come out with the ball at his feet and "scream at me to get back in goal. I've never stopped to think about what others are saying. I just rely on my abilities. Later on, I started to practice penalties and free kicks until they gave me the job for real".[11] Chilavert admitted to staying behind after training to practice 80 to 120 free kicks, which in his opinion was how he got better.[3]

Chilavert refused to take part in the 1999 Copa América, angering the Paraguayan government, as he claimed funding should be used for education.[21]

FIFA gave Chilavert a four-game suspension (later reduced to three) for spitting on Brazil's Roberto Carlos at the conclusion of a 2002 FIFA World Cup qualification game. As a result, he watched Paraguay's first game of the 2002 World Cup against South Africa from the stands.[18] Chilavert accused Roberto Carlos of racism and of making obscene gestures during the match.[14] Chilavert later claimed that Roberto Carlos came up to him after the match and said "Indian, we have won 2–0, you are a disaster".[22] He also justified his action by saying he had been provoked by the Brazilians, who had called him the weakest link of Paraguay before the match, and also claimed the match was like a war and that Brazil should return land to Paraguay lost in the War of the Triple Alliance in the 19th century.[22]

Before the 2002 FIFA World Cup, Paraguay manager Cesare Maldini had faced criticism in Paraguay, but Chilavert defended Maldini for his experience.[23] He also expressed great confidence in the ability of the Paraguayan team and downplayed his role on the team.[24] During the World Cup, Chilavert made an error against Spain on Morientes's 2–1 goal as Paraguay lost 3–1. Chilavert almost redeemed himself later with a good free kick attempt, but the shot was saved by Casillas.[25] Before the match, Chilavert had vowed to score against Spain if Paraguay got a free kick "within range".[26] Before the last match in the group stage, Paraguay had to beat Slovenia and Spain had to beat South Africa, with a combined margin of three goals, for Paraguay to go through to the last 16. The match started badly for Paraguay, with Carlos Paredes sent off in the 21st minute, and continued with Milenko Ačimovič taking the lead for the Slovenians right before half-time. But Paraguay – inspired by substitutes Nelson Cuevas and Jorge Campos – recovered to defeat Slovenia 3–1, scoring three times in the last 25 minutes, and when Spain also defeated South Africa 3–2, that victory meant that Paraguay was through to the next round, where they would play Germany.[27][28] In their second-round match against Germany, despite several saves from Chilavert, Paraguay lost 1–0, courtesy of a late Oliver Neuville goal.[14][29]

In total, Chilavert earned 74 international caps for Paraguay and achieved a goalkeeper record of eight international goals.[citation needed] He retired from international football in 2003.[30]

Chilavert announced his retirement from football in December 2003, but decided to come out of retirement to return to Vélez. Chilavert had just won the Uruguayan league with Peñarol when he initially retired. He finally retired permanently in 2004, playing his last match, a farewell testimonial, on November 11 of that year – fittingly, he scored a goal.[31]

In 2005, Chilavert received a suspended six-month prison sentence in France for the use of false documents related to the compensation for the end of his contract with Strasbourg.[32]

Chilavert has allegedly thrown punches at Faustino Asprilla and Diego Maradona.[34] He was suspended for four matches for his altercation with the former that occurred during a World Cup qualifier in 1997.[35]

He once received a suspended prison sentence for attacking a physiotherapist.[3]

Chilavert defended Cesare Maldini from the members of the Paraguayan press who criticized Maldini when he was appointed as Paraguay's coach for the 2002 FIFA World Cup. Chilavert stated that "About 90% of sports journalists in Paraguay are incompetent" and welcomed criticism following Paraguay's performance in Korea and Japan if they were to perform poorly.[38]

During his career, Chilavert was being touted as Paraguay's future president.[34] Chilavert was labelled "a revolutionary the kind of which South America has not seen since the days of Che Guevara."[34]

Off the field, Chilavert refused to participate at the 1999 Copa América, held in Paraguay, complaining about the incompetence of the local directors. Despite being officially honored by the government, he said that his country should invest money in education rather than football.[39][40] Chilavert also routinely dismissed his country's politicians as corrupt, incompetent, and responsible for keeping many Paraguayans in poverty. Chilavert claimed that when his playing days were over, he would stand for president and enforce his own brand of law and order.[40]

During 2008 and 2009, the former goal keeper demonstrated his support for Paraguayan Olympic thrower Edgar Baumann against corruption in Paraguayan sport when the athlete had been robbed of his right to compete at the 2000 Sydney Olympics due to a scandal from the Paraguayan Olympic Committee. Chilavert supported Baumann during the lawsuit which had been filed against the Olympic Committee with Chilavert stated that the then president of the Olympic Committee, Ramón Zubizarreta, should be expulsed for hurting athletes and not giving them benefits.[41][42][43]

In 2009, Chilavert, along with Claudio Escauriza, Tomás Orué and lawyer Alejandro Rubin, attended a Press Conference at Asunción Shopping Centre Shopping del Sol, in support Edgar Baumann, who had received a favorable ruling from the Paraguay Supreme Court in a case against the Paraguay Olympic Committee president Ramón Zubizarreta for robbing him the right of competing at the 2000 Summer Olympics and also taking his sums of money that he earned from his scholarship.[44]